Reactions of an isolable dialkylsilylene with aromatic nitriles providing a new type of heterosilole
Liliang Wang1, Weifeng Chen, Zhifang Li
1Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, 310012, China. zhifanglee@hznu.edu.cn mkira@m.tohoku.ac.jp.
Abstract:
The 1 : 2 reactions of isolable dialkylsilylene with nitriles having electron-donating aromatic substituents gave 1,4-diaza-2-siloles with a hitherto-unknown type of ring system, in contrast to the previous studies showing exclusive formation of the corresponding 1,3-diaza-2-siloles; the reactions of with aromatic nitriles bearing electron-withdrawing substituents afforded the latter ring system. The remarkable diversity of the reactions is explained by invoking the corresponding nitrile silaylides as key intermediates whose polarity switches depending on the substituents of nitriles.
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